This application is a 317 of PCT/EP98/00972 filed Feb. 20, 1998.
The invention relates to new substituted aromatic amino compounds, the processes for their preparation, and to their use as herbicides.
Some substituted aromatic amino compounds such as, for example, N-[2-(1,5-dihydro-1-methyl-5-thioxo-3-trifluoromethyl-4H-1,2,4-triazol-4-yl)-5-fluorophen-yl]-benzamide and N-[5-chloro-2-(1,5-dihydro-1-methyl-5-thioxo-3-trifluoromethyl-4H-1,2,4-triazol-4-yl)-phenyl]-acetamide have already been disclosed in the patent literature as candidate herbicides (cf. U.S. Pat. No. 5,108,486). However, these compounds have not gained any particular importance.
Other substituted aromatic amino compounds such as, for example, N-[5-chloro-2-(2,5-dihydro-3,4-dimethyl-2,5-dioxo-1H-pyrrol-1-yl)-phenyl]-acetamide (cf. Indian J. Chem, Sect. B, 29B (1990), 659-660xe2x80x94cited in Chem. Abstracts 113:211906) and N-[2-(5-diethylamino-3-t-butyl-1H-1,2,4-triazol-1-yl)-5-trifluoromethyl-phenyl]-2,2-dimethyl-propanamide and N-[2-(5-diethylamino-3-t-butyl-1H-1,2,4-triazol-1-yl)-5-trifluoromethyl-phenyl]-acetamide (cf. JP 02091062xe2x80x94cited in Chem. Abstracts 113:97612) are also known already. However, nothing has been disclosed about the herbicidal activity of these compounds.
There have now been found new substituted aromatic amino compounds of the general formula (I) 
in which
R1 represents hydrogen, hydroxyl, amino, alkyl, alkoxy, alkylamino or dialkylamino, or represents one of the groups which follow,
xe2x80x94CQ1xe2x80x94R5, xe2x80x94CQ1xe2x80x94Q2xe2x80x94R6, xe2x80x94S(O)nxe2x80x94R7,
R2 represents one of the groups which follow,
xe2x80x94CQ1xe2x80x94R5, xe2x80x94CQ1xe2x80x94Q2xe2x80x94R6, xe2x80x94S(O)nxe2x80x94R7,
R3 represents hydrogen, hydroxyl, amino, carboxyl, cyano, carbamoyl, thiocarbamoyl, nitro, halogen, in each case optionally substituted alkyl, alkoxy, alkoxycarbonyl, alkylthio, alkylsulphinyl or alkylsulphonyl, or one of the groups which follow,
xe2x80x94SO2xe2x80x94NHxe2x80x94R5, xe2x80x94NHxe2x80x94SO2xe2x80x94R7, xe2x80x94N(SO2xe2x80x94R7)2, xe2x80x94N(SO2xe2x80x94R7)(COxe2x80x94R5),
R4 represents hydrogen, hydroxyl, amino, carboxyl, cyano, carbamoyl, thiocarbamoyl, nitro, halogen, in each case optionally substituted alkyl, alkoxy, alkoxycarbonyl, alkylthio, alkylsulphinyl or alkylsulphonyl, or one of the groups which follow,
xe2x80x94SO2xe2x80x94NHxe2x80x94R5, xe2x80x94NH-SO2xe2x80x94R7, xe2x80x94N(SO2xe2x80x94R7)2, xe2x80x94N(SO2xe2x80x94R7)(COxe2x80x94R5),
n represents the numbers 0, 1 or 2,
Q1 represents O or S and
Q2 represents O, S, NH or N-alkyl,
R5 represents hydrogen or in each case optionally substituted alkyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl or heterocyclyl,
R6 represents in each case optionally substituted alkyl, alkenyl, alkinyl, cycloalkyl, cycloalkylalkyl, aryl or arylalkyl,
R7 represents in each case optionally substituted alkyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl or heterocyclyl, and
Z represents one of the heterocyclic groups which follow 
xe2x80x83where in each case
Q1 and Q2 have the abovementioned meaning,
R8 represents hydrogen, amino, nitro, cyano, carboxyl, carbamoyl, thiocarbamoyl, halogen, or in each case optionally substituted alkyl, alkenyl, alkinyl, alkoxy, alkoxycarbonyl, alkenyloxy, alkinyloxy, alkylthio, alkenylthio, alkinylthio, alkylamino, dialkylamino, cycloalkyl or cycloalkylalkyl, and
R9 represents hydrogen, hydroxyl, amino, cyano, or in each case optionally substituted alkyl, alkenyl, alkinyl, alkoxycarbonyl, cycloalkyl, cycloalkylalkyl, phenyl or phenylalkyl,
where, if appropriate, two adjacent radicalsxe2x80x94R8 and R8, R9 and R9 or R8 and R9xe2x80x94together represent alkanediyl (alkylene) or oxaalkanediyl, and
where the individual radicals R8 and R9xe2x80x94if they occur more than once in the same heterocyclic group, may have identical or different meanings within the scope of the above definition,
with the exception of the prior-art compound N-[5-chloro-2-(2,5-dihydro-3,4-dimethyl-2,5-dioxo-1H-pyrrol-1-yl)-phenyl]-acetamide (cf. Indian J. Chem, Sect. B, 29B (1990), 659-660xe2x80x94cited in Chem. Abstracts 113:211906), and of N-[2-(5-diethylamino-3-t-butyl-1H-1,2,4-triazol-1-yl)-5-trifluoromethyl-pheny]-2,2-dimethyl-propanamide and N-[2-(5-diethylamino-3-t-butyl-1H-1,2,4-triazol-1-yl)-5-trifluoromethyl-phenyl]-acetamide (cf. JP 02091062xe2x80x94cited in Chem. Abstracts 113:97612), which are also prior-art compounds.
The new substituted aromatic amino compounds of the general formula (I) are obtained when aromatic amino compounds of the general formula (II) 
in which
R3, R4 and Z have the abovementioned meaning and
A1 represents hydrogen, hydroxyl, amino, alkyl, alkoxy, alkylamino or dialkylamino
are reacted with electrophilic compounds of the general formula (III)
Xxe2x80x94R2xe2x80x83xe2x80x83(III)
in which
R2 has the abovementioned meaning and
X represents halogen,
if appropriate in the presence of an acid acceptor and if appropriate in the presence of a diluent,
and the resulting compounds of the general formula (I) are converted into other compounds of the general formula (I) in accordance with the above definition (cf. the preparation examples), if appropriate by customary methods.
The new substituted aromatic amino compounds of the general formula are distinguished by a potent and selective herbicidal activity.
In the definitions, the saturated or unsaturated hydrocarbon chains, such as alkyl, alkanediyl, alkenyl or alkinylxe2x80x94also in connection with hetero atoms, such as in alkoxy, alkylthio or alkylaminoxe2x80x94are in each case straight-chain or branched.
Halogen generally represents fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine, in particular fluorine or chlorine.
The invention preferably relates to compounds of the formula (I)
in which
R1 represents hydrogen, hydroxyl, amino, or represents alkyl, alkoxy, alkylamino or dialkylamino, each of which has 1 to 6 carbon atoms in the alkyl groups, or represents one of the groups which follow,
xe2x80x83xe2x80x94CQ1xe2x80x94R5, xe2x80x94CQ1xe2x80x94Q2xe2x80x94R6, xe2x80x94S(O)nxe2x80x94R7,
R2 represents one of the groups which follow,
xe2x80x94CQ1xe2x80x94R5, xe2x80x94CQ1xe2x80x94Q2xe2x80x94R6, xe2x80x94S(O)nxe2x80x94R7,
R3 represents hydrogen, hydroxyl, amino, carboxyl, cyano, carbamoyl, thiocarbamoyl, nitro, halogen, or represents alkyl, alkoxy, alkoxycarbonyl, alkylthio, alkylsulphinyl or alkylsulphonyl, each of which has 1 to 6 carbon atoms in the alkyl groups and each of which is optionally substituted by cyano, halogen or C1-C4-alkoxy, or represents one of the groups which follow,
xe2x80x94SO2xe2x80x94NHxe2x80x94R5, xe2x80x94NHxe2x80x94SO2xe2x80x94R7, xe2x80x94N(SO2xe2x80x94R7)2, xe2x80x94N(SO2xe2x80x94R7)(COxe2x80x94R5),
R4 represents hydrogen, hydroxyl, amino, carboxyl, cyano, carbamoyl, thiocarbamoyl, nitro, halogen, or represents alkyl, alkoxy, alkoxycarbonyl, alkylthio, alkylsulphinyl or alkylsulphonyl, each of which has 1 to 6 carbon atoms in the alkyl groups and each of which is optionally substitued by cyano, halogen or C1-C4-alkoxy, or represents one of the groups which follow,
xe2x80x94SO2xe2x80x94NHxe2x80x94R5, xe2x80x94NHxe2x80x94SO2xe2x80x94R7, xe2x80x94N(SO2xe2x80x94R7)2, xe2x80x94N(SO2xe2x80x94R7)(COxe2x80x94R5),
n represents the numbers 0, 1 or 2,
Q1 represents O or S and
Q2 represents O, S, NH or N-alkyl having 1 to 4 carbon atoms,
R5 represents hydrogen, or represents alkyl which has 1 to 6 carbon atoms and which is optionally substituted by cyano, halogen or C1-C4-alkoxy, or represents cycloalkyl or cycloalkylalkyl, each of which has 3 to 6 carbon atoms in the cycloalkyl group and, if appropriate, 1 to 4 carbon atoms in the alkyl moiety and each of which is optionally substituted by cyano, halogen or C1-C4-alkyl, or represents aryl or arylalkyl, each of which has 6 or 10 carbon atoms in the aryl group and, where appropriate, 1 to 4 carbon atoms in the alkyl moiety and each of which is optionally substituted by cyano, nitro, halogen, C1-C4-alkyl, C1-C4-halogenoalkyl, C1-C4-alkoxy or C1-C4-halogenoalkoxy, or represents heterocyclyl which is optionally substituted by halogen, C1-C4-alkyl, C1-C4-halogenoalkyl, C1-C4-alkoxy or C1-C4-halogenoalkoxy, preferred heterocyclyl groups being furyl, tetrahydrofuryl, thienyl, pyridyl and pyrimidinyl,
R6 represents alkyl which has 1 to 6 carbon atoms and which is optionally substituted by cyano, halogen or C1-C4-alkoxy, or represents alkenyl or alkinyl, each of which has 2 to 6 carbon atoms and each of which is optionally substituted by halogen, or represents cycloalkyl or cycloalkylalkyl, each of which has 3 to 6 carbon atoms in the cycloalkyl group and, if appropriate, 1 to 4 carbon atoms in the alkyl moiety and each of which is optionally substituted by cyano, halogen or C1-C4-alkyl, or represents aryl or arylalkyl, each of which has 6 or 10 carbon atoms in the aryl group and, if appropriate, 1 to 4 carbon atoms in the alkyl moiety and each of which is optionally substituted by cyano, nitro, halogen, C1-C4-alkyl, C1-C4-halogenoalkyl, C1-C4-alkoxy or C1-C4-halogenoalkoxy,
R7 represents alkyl which has 1 to 6 carbon atoms and which is optionally subsituted by halogen, or represents cycloalkyl or cycloalkylalkyl, each of which has 3 to 6 carbon atoms in the cycloalkyl moiety and, if appropriate, 1 to 4 carbon atoms in the alkyl moiety and each of which is optionally substituted by halogen, or represents aryl or arylalkyl, each of which has 6 or 10 carbon atoms in the aryl group and, if appropriate, 1 to 4 carbon atoms in the alkyl moiety and each of which is optionally substituted by cyano, nitro, halogen, C1-C4-alkyl, C1-C4-halogenoalkyl, C1-C4-alkoxy, C1-C4-halogenoalkoxy, C1-C4-alkylthio, C1-C4-alkylsulphinyl, C1-C4-alkylsulphonyl or C1-C4-alkoxy-carbonyl, or represents heterocyclyi which is optionally substituted by halogen, C1-C4-alkyl, C1-C4-halogenoalkyl, C1-C4-alkoxy or C1-C4-halogenoalkoxy, preferred heterocyclyl groups being pyridyl and pyrimidinyl, and
Z represents one of the heterocyclic groups which follow 
xe2x80x83where in each case
Q1 and Q2 have the abovementioned meaning,
R8 represents hydrogen, amino, nitro, cyano, carboxyl, carbamoyl, thiocarbamoyl, halogen, or represents alkyl which has 1 to 6 carbon atoms and which is optionally substituted by cyano, halogen or C1-C4-alkoxy, or represents alkenyl or alkinyl, each of which has 2 to 6 carbon atoms and each of which is optionally substituted by halogen, or represents alkoxy or alkoxycarbonyl, each of which has 1 to 6 carbon atoms in the alkyl groups and each of which is optionally substituted by cyano, halogen or C1-C4-alkoxy, or represents alkenyloxy or alkinyloxy, each of which has 3 to 6 carbon atoms and each of which is optionally substituted by halogen, or represents alkylthio which has 1 to 6 carbon atoms and which is optionally substituted by cyano, halogen or C1-C4-alkoxy, or represents alkenylthio or alkinylthio, each of which has 3 to 6 carbon atoms and each of which is optionally substituted by halogen, or represents alkylamino or dialkylamino, each of which has 1 to 6 carbon atoms in the alkyl groups each of which is optionally substituted by cyano, halogen or C1-C4-alkoxy, or represents cycloalkyl or cycloalkylalkyl, each of which has 3 to 6 carbon atoms in the cycloalkyl groups and, if appropriate, 1 to 4 carbon atoms in the alkyl moiety and each of which is optionally substituted by cyano, halogen or C1-C4-alkyl, and
R9 represents hydrogen, hydroxyl, amino, cyano, or represents alkyl which has 1 to 6 carbon atoms and which is optionally substituted by cyano, halogen or C1-C4-alkoxy, or represents alkenyl or alkinyl, each of which has 2 to 6 carbon atoms and which is optionally substituted by halogen, or represents alkoxycarbonyl, which is optionally substituted by cyano, halogen or C1-C4-alkoxy, or represents cycloalkyl or cycloalkylalkyl, each of which has 3 to 6 carbon atoms in the cycloalkyl groups and, if appropriate, 1 to 4 carbon atoms in the alkyl moiety and each of which is optionally substituted by cyano, halogen or C1-C4-alkyl, or represents phenyl or phenyl-C1-C4-alkyl, each of which is optionally substituted by cyano, nitro, halogen, C1-C4-alkyl, C1-C4-halogenoalkyl, C1-C4-alkoxy and/or C1-C4-halogenoalkoxy,
where, if appropriate, two adjacent radicalsxe2x80x94R8 and R8, R9 and R9 or R8 and R9xe2x80x94together represent alkanediyl (alkylene) or oxaalkanediyl having in each case 2 to 6 carbon atoms, and
where the individual radicals R8 and R9xe2x80x94if they occur more than once in the same heterocyclic group, may have identical or different meanings within the above definition,
with the exception of the prior-art compound N-[5-chloro-2-(2,5-dihydro-3,4-dimethyl-2,5-dioxo-1H-pyrrol-1-yl)-phenyl]-acetamide (cf. Indian J. Chem, Sect. B, 29B (1990), 659-660xe2x80x94cited in Chem. Abstracts 113:211906), and of N-[2-(5-diethylamino-3-t-butyl-1H-1,2,4-triazol-1-yl)-5-trifluoromethyl-phenyl]-2,2-dimethyl-propanamide and N-[2-(5-diethylamino-3-t-butyl-1H-1,2,4-triazol-1-yl)-5-trifluoromethyl-phenyl]-acetamide (cf. JP 02091062xe2x80x94cited in Chem. Abstracts 113:97612), which are also prior-art compounds.
The invention particularly relates to compounds of the formula (I) in which
R1 represents hydrogen, hydroxyl, amino, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino or dimethylamino, or one of the groups which follow,
xe2x80x94CQ1xe2x80x94R5, xe2x80x94CQ1xe2x80x94Q2xe2x80x94R6, xe2x80x94S(O)nxe2x80x94R7,
R2 represents one of the groups which follow,
xe2x80x94CQ1xe2x80x94R5, xe2x80x94CQ1xe2x80x94Q2xe2x80x94R6, xe2x80x94S(O)nxe2x80x94R7,
R3 represents hydrogen, hydroxyl, amino, carboxyl, cyano, carbamoyl, thiocarbamoyl, nitro, fluorine, chlorine, bromine, or represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methoxycarbonyl, ethoxycarbonyl, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylsulphinyl, ethylsulphinyl, methylsulphonyl or ethylsulphonyl, each of which is optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy, or represents one of the groups which follow,
xe2x80x94SO2xe2x80x94NHxe2x80x94R5, xe2x80x94NHxe2x80x94SO2xe2x80x94R7, xe2x80x94N(SO2xe2x80x94R7)2, xe2x80x94N(SO2xe2x80x94R7)(COxe2x80x94R5),
R4 represents hydrogen, hydroxyl, amino, carboxyl, cyano, carbamoyl, thiocarbamoyl, nitro, fluorine, chlorine, bromine, or represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methoxycarbonyl, ethoxycarbonyl, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylsulphinyl, ethylsulphinyl, methylsulphonyl or ethylsulphonyl, each of which is optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy, or represents one of the groups which follow,
xe2x80x94SO2xe2x80x94NHxe2x80x94R5, xe2x80x94NHxe2x80x94SO2xe2x80x94R7, xe2x80x94N(SO2xe2x80x94R7)2, xe2x80x94N(SO2xe2x80x94R7)(COxe2x80x94R5),
n represents the numbers 0, 1 or 2,
Q1 represents O or S and
Q2 represents O, S, NH or N-methyl,
R5 represents hydrogen, or represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, each of which is optionally substituted by cyano, fluorine, chlorine, bromine, methoxy or ethoxy, or represents cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl, each of which is optionally substituted by cyano, fluorine, chlorine, bromine, methyl or ethyl, or represents phenyl or benzyl, each of which is optionally substituted by cyano, nitro, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, difluoromethoxy or trifluoromethoxy, or represents furyl, tetrahydrofuryl, thienyl or pyridyl, each of which is optionally substituted by fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, difluoromethoxy or trifluoromethoxy,
R6 represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, each of which is optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy, or represents propenyl, butenyl, propinyl or butinyl, each of which is optionally substituted by fluorine, chlorine or bromine, or represents cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl, each of which is optionally substituted by cyano, fluorine, chlorine, bromine, methyl or ethyl, or represents phenyl or benzyl, each of which is optionally substituted by cyano, nitro, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, difluoromethoxy or trifluoromethoxy,
R7 represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, each of which is optionally substituted by fluorine, chlorine or bromine, or represents cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl, each of which is optionally substituted by fluorine, chlorine or bromine, or represents phenyl or benzyl, each of which is optionally substituted by cyano, nitro, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, difluoromethoxy, trifluoromethoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylsulphinyl, ethylsulphinyl, methylsulphonyl, ethylsulphonyl, methoxycarbonyl or ethoxy-carbonyl or represents pyridyl or pyrimidinyl, each of which is optionally substituted by fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, difluoromethoxy, and
Z represents one of the heterocyclic groups which follow 
xe2x80x83where in each case
Q1 and Q2 have the abovementioned meaning,
R8 represents hydrogen, amino, nitro, cyano, carboxyl, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, or represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, each of which is optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy, or represents propenyl, butenyl, propinyl or butinyl, each of which is optionally substituted by fluorine, chlorine or bromine, or represents methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methoxycarbonyl or ethoxycarbonyl, each of which is optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy, or represents propenyloxy, butenyloxy, propinyloxy or butinyloxy, each of which is optionally substituted by fluorine or chlorine, or represents methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, each of which is optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy, or represents propenylthio, butenylthio, propinylthio or butinylthio, each of which is optionally substituted by fluorine or chlorine, or represents methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, dimethylamino or diethylamino, each of which is optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy, or represents cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl, each of which is optionally substituted by cyano, fluorine, chlorine, bromine, methyl or ethyl, and
R9 represents hydrogen, hydroxyl, amino, cyano, or represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, each of which is optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy, or represents propenyl, butenyl, propinyl or butinyl, each of which is optionally substituted by fluorine, chlorine or bromine, or represents methoxycarbonyl or ethoxycarbonyl, each of which is optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy, or represents cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl, each of which is optionally substituted by cyano, fluorine, chlorine, bromine, methyl or ethyl, or represents phenyl or benzyl, each of which is optionally substituted by cyano, nitro, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, difluoromethoxy and/or trifluoromethoxy,
where, if appropriate, two adjacent radicalsxe2x80x94R8 and R8, R9 and R9 or R8 and R9xe2x80x94together represent ethane-1,2-diyl (dimethylene), propane-1,3-diyl (trimethylene), butane-1,4-diyl (tetramethylene) or 1-oxa-butane-1,4-diyl, and
where the individual radicals R8 and R9xe2x80x94if they occur more than once in the same heterocyclic group, may have identical or different meanings within the above definition,
with the exception of the prior-art compound N-[5-chloro-2-(2,5-dihydro-3,4-dimethyl-2,5-dioxo-1H-pyrrol-1-yl)-phenyl]-acetamide (cf. Indian J. Chem, Sect. B, 29B (1990), 659-660xe2x80x94cited in Chem. Abstracts 113:211906), and of N-[2-(5-diethylamino-3-t-butyl-1H-1,2,4-triazol-1-yl)-5-trifluoromethyl-phenyl]-2,2-dimethyl-propanamide and N-[2-(5-diethylamino-3-t-butyl-1H-1,2,4-triazol-1-yl)-5-trifluoromethyl-phenyl]-acetamide (cf. JP 02091062xe2x80x94cited in Chem. Abstracts 113:97612), which are also prior-art compounds.
Very especially preferred are those compounds of the formula (I)
in which
R1, R2, R3, R4, n, Q1, Q2, R5, R6 and R7 have the meanings given above as being particularly preferred and
Z represents one of the heterocyclic groups which follow. 
xe2x80x83where in each case
Q1, Q2, R8 and R9 have the meanings given above as being particularly preferred.
The abovementioned general definitions of radicals, or definitions of radicals where preferred ranges have been given, apply to the end products of the formula (I) and, analogously, to the starting materials or intermediates required in each case for the preparation. These definitions of radicals can be combined with each other as desired, that is to say combinations between the preferred ranges given are also possible.
Examples of the compounds of the formula (I) according to the invention are given in the groups which follow. 
R1, R2, R3 and R4 have the meanings given in the list which follows:

R1, R2 R3 and R4 have, by way of example, the meanings given above in Group 1. 
R1, R2 R3 and R4 have, by way of example, the meanings given above in Group 1.
R1, R2 R3 and R4 have, by way of example, the meanings given above in Group 1.
R1, R2 R3 and R4 have, by way of example, the meanings given above in Group 1.
R1, R2 R3 and R4 have, by way of example, the meanings given above in Group 1.
R1, R2 R3 and R4 have, by way of example, the meanings given above in Group 1.
R1, R2 R3 and R4 have, by way of example, the meanings given above in Group 1.
R1, R2 R3 and R4 have, by way of example, the meanings given above in Group 1.
R1, R2 R3 and R4 have, by way of example, the meanings given above in Group 1.
R1, R2 R3 and R4 have, by way of example, the meanings given above in Group 1.
R1, R2 R3 and R4 have, by way of example, the meanings given above in Group 1.
R1, R2 R3 and R4 have, by way of example, the meanings given above in Group 1. 
R1, R2 R3 and R4 have, by way of example, the meanings given above in Group 1.
R1, R2 R3 and R4 have, by way of example, the meanings given above in Group 1.
If, for example, 2-(2-amino-4-cyano-phenyl)-4-methyl-5-difluoromethyl-2,4-dihy-dro-3H-1,2,4-triazol-3-one and acetyl chloride are used as starting materials, the course of the reaction in the process according to the invention can be outlined by the following scheme: 
Formula (II) provides the general definition of the aromatic amino compounds to be used as starting materials in the process according to the invention for the preparation of compounds of the formula (I). In formula (II), R3, R4 and Z preferably, or in particular, have those meanings which have already been mentioned above in connection with the description of the compounds of the formula (I) according to the invention as being preferred, or particularly preferred, for R3, R4 and Z; A1 preferably represents hydrogen, hydroxyl, amino, C1-C6-alkyl, C1-C6-alkoxy, C1-C6-alkylamino or di-(C1-C6-alkyl)-amino, in particular hydrogen or methyl.
The starting materials of the general formula (II) were hitherto unknown from the literature; being new substances, they are also a subject of the present application.
The new aromatic amino compounds of the general formula (II) are obtained when aromatic nitro compounds of the general formula (IV) 
in which
R3, R4 and Z have the abovementioned meaning
are reacted with reducing agents such as, for example, with hydrogen in the presence of a catalyst, such as, for example, Raney nickel, or with tin(lI) chloride dihydrate, or with iron in the presence of an acid such as, for example, hydrochloric acid, in each case in the presence of a diluent such as, for example, water, methanol or ethanol, at temperatures between 0xc2x0 C. and 120xc2x0 C. (cf. the preparation examples).
The aromatic nitro compounds of the general formula (IV) which are required as precursors are known and/or can be prepared by known processes (cf. U.S. Pat. No. 3,489,761, DE 2413938, GB 2123420, U.S. Pat. No. 4,496,390, WO 8702357, EP 617026, preparation examples).
Formula (III) provides a general definition of the electrophilic compounds furthermore to be used as starting materials in the process according to the invention for the preparation of compounds of the formula (I). In formula (III), R2 preferably, or in particular, has the meaning which has already been given above in connection with the description of the compounds of the formula (I) according to the invention as preferred, or particularly preferred, for R2; X preferably represents fluorine, chlorine, bromine or iodine, in particular chlorine or bromine.
The starting materials of the general formula (III) are known chemicals for organic synthesis.
The process according to the invention for the preparation of the compounds of the formula (I) is preferably carried out using an acid acceptor. Suitable acid acceptors for the process according to the invention are, generally, the customary inorganic or organic bases or acid binders. These preferably include acetates, amides, carbonates, hydrogen carbonates, hydrides, hydroxides or alkanolates of alkali metals or alkaline earth meals, such as, for example, sodium acetate, potassium acetate, calcium acetate, lithium amide, sodium amide, potassium amide or calcium amide, sodium carbonate, potassium carbonate or calcium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, calcium hydrogen carbonate, lithium hydride, sodium hydride, potassium hydride, calcium hydride, lithium hydroxide, sodium hydroxide, potassium hydroxide, calcium hydroxide, sodium methoxide, sodium ethoxide, sodium n- or i-propoxide, sodium n-, i-, s- or t-butoxide, potassium methoxide, potassium ethoxide, potassium n- or i-propoxide or potassium n-, i-, s- or t-butoxide; furthermore also basic organic nitrogen compounds such as, for example, trimethylamine, triethylamine, tripropylamine, tributylamine, ethyl-diisopropylamine, N,N-dimethyl-cyclohexylamine, dicyclohexylamine, ethyl-dicyclohexylamine, N,N-dimethyl-aniline, N,N-dimethyl-benzylamine, pyridine, 2-methyl-, 3-methyl-, 4-methyl-, 2,4-dimethyl-, 2,6-dimethyl-, 3,4-dimethyl- and 3,5-dimethyl-pyridine, 5-ethyl-2-methyl-pyridine, 4-dimethylamino-pyridine, N-methyl-piperidine, 1,4-diazabicyclo[2,2,2]-octane (DABCO), 1,5-diazabicyclo[4,3,0]-non-5-ene (DBN), or 1,8-diazabicyclo[5,4,0]-undec-7-ene (DBU).
The process according to the invention for the preparation of the compounds of the formula (I) is preferably carried out using a diluent. Suitable diluents for carrying out the process according to the invention are, especially, inert organic solvents. These include, in particular, aliphatic, alicyclic or aromatic, optionally halogenated hydrocarbons such as, for example, benzine, benzene, toluene, xylene, chlorobenzene, dichlorobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, chloroform, carbon tetrachloride; ethers such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran, ethylene glycol dimethyl ether or ethylene glycol diethyl ether; ketones, such as acetone, butanone or methyl isobutyl ketone; nitriles such as acetonitrile, propionitrile or butyronitrile; amides such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-formanilide, N-methyl-pyrrolidone or hexamethylphosphoric triamide; esters such as methyl acetate or ethyl acetate, sulphoxides such as dimethyl sulphoxide, alcohols such as methanol, ethanol, n- or i-propanol, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, their mixtures with water, or pure water.
When carrying out the process according to the invention, the reaction temperatures may be varied within a substantial range. In general, the process is carried out at temperatures between 0xc2x0 C. and 150xc2x0 C., preferably between 10xc2x0 C. and 120xc2x0 C.
The process according to the invention is generally carried out under atmospheric pressure. However, it is also possible to carry out the process according to the invention under elevated or reduced pressure, in general between 0.1 bar and 10 bar.
To carry out the process according to the invention, the starting materials are generally employed in approximately equimolar amounts. However, it is also possible to use one of the components in a larger excess. In general, the reaction is carried out in a suitable diluent in the presence of a reaction auxiliary, and the reaction mixture is generally stirred for several hours at the temperature required. Working-up is carried out by customary methods (cf. the preparation examples).
The active compounds according to the invention can be used as defoliants, desiccants, haulm killers and, in particular, as herbicides. Weeds in the broadest sense are to be understood as meaning all plants which are grown in locations where they are undesired. Whether the substances according to the invention act as total or selective herbicides depends essentially on the quantity applied.
The active compounds according to the invention can be used, for example, on the following plants:
Dicotyledonous weeds of the genera: Sinapis, Lepidium, Galium, Stellaria, Matricaria, Anthemis, Galinsoga, Chenopodium, Urtica, Senecio, Amaranthus, Portulaca, Xanthium, Convolvulus, Ipomoea, Polygonum, Sesbania, Ambrosia, Cirsium, Carduus, Sonchus, Solanum, Rorippa, Rotala, Lindemia, ILamium, Veronica, Abutilon, Emex, Datura, Viola, Galeopsis, Papaver, Centaurea, Trifolium, Ranunculus, Taraxacum.
Dicotyledonous crops of the genera: Gossypium, Glycine, Beta, Daucus, Phaseoltis, Pisum, Solanum, Linum, lpomoea, Vicia, Nicotiana, Lycopersicon, Arachis, Brassica, Lactuca, Cucumis, Cucurbita.
Monocotyledonous weeds of the genera: Echinochloa, Setaria, Panicum, Digitaria, Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium, Bromus, Avena, Cyperus, Sorghum, Agropyron, Cynodon, Monochoria, Fimbristylis, Sagittaria, Eleocharis, Scirpus, Paspalum, Ischaemum, Sphenoclea, Dactyloctenium, Agrostis, Alopecurus, Apera.
Monocotyledonous crops of the genera: Oryza, Zea, Triticum, Hordeum, Avena, Secale, Sorghum, Panicum, Saccharum, Ananas, Asparagus, Allium.
However, the use of the active compounds according to the invention is in no way restricted to these genera, but equally extends to other plants.
Depending on the concentration, the compounds are suitable for the total control of weeds on, for example, industrial terrain and rail tracks and on paths and squares with or without tree plantings. Equally, the compounds may be employed for controlling weeds in perennial crops, for example afforestations, plantings of woody ornamentals, orchards, vineyards, citrus orchards, nut orchards, banana plantations, coffee plantations, tea plantations, rubber plantations, oil palm plantations, cocoa plantations, soft fruit plantings, hop plantings, on ornamental lawns, turf and pastures, and for the selective control of weeds in annual crops.
The compounds of the formula (I) according to the invention are particularly suitable for the selective control of monocotyledonous and dicotyledonous weeds in monocotyledonous crops such as, for example, in wheat, both pre- and post-emergence.
The active compounds can be converted into the customary formulations such as solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspoemulsion concentrates, natural and synthetic products impregnated with active compound, and microencapsulations in polymeric substances.
These formulations are prepared in the known manner, for example by mixing the active compounds with extenders, that is to say liquid solvents and/or solid carriers, if appropriate using surfactants, that is to say emulsifiers and/or dispersants and/or foam formers.
If water is used as extender, it is also possible, for example, to use organic solvents as auxiliary solvents. Suitable liquid solvents are essentially: aromatics such as xylene, toluene, or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane, or paraffins, for example mineral oil fractions, mineral and vegetable oils, alcohols such as butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulphoxide, and water.
Examples of suitable solid carriers are: ammonium salts and ground natural minerals such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals such as highly disperse silica, alumina and silicates; suitable solid carriers for granules are: for example crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite, and synthetic granules of inorganic or organic meals and granules of organic material such as sawdust, coconut shells, maize cobs and tobacco stalks; suitable emulsifiers and/or foam formers are: for example non-ionic and anionic emulsifiers such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkylsulphonates, alkyl sulphates, arylsulphonates and protein hydrolysates; suitable dispersants are: for example lignin-sulphite waste liquors and methylcellulose.
Adhesives such as carboxymethylcellulose, natural and synthetic polymers in the form of powders, granules or latices such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospholipids such as cephalins and lecithins and synthetic phospholipids may be used in the formulations. Other additives may be mineral and vegetable oils.
Colorants such as inorganic pigments, for example iron oxide, titanium oxide, Prussian Blue, and organic dyestuffs such as alizarin, azo and metal phthalocyanin dyes and micronutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc may be used.
The formulations generally comprise between 0.1 and 95% by weight of active compound, preferably between 0.5 and 90%.
The active compounds according to the invention, as such, or in their formulations, may also be used for controlling weeds as a mixture with known herbicides, readymixes or tank mixes being possible.
Suitable known herbicides for the mixtures are, for example
acetochlor, acifluorfen(-sodium), aclonifen, alachlor, alloxydim(-sodium), ametryne, amidochlor, amidosulphuron, asulam, atrazine, azimsulphuron, benazolin, benfuresate, bensulphuron(-methyl), bentazone, benzofenap, benzoylprop(-ethyl), bialaphos, bifenox, bromobutide, bromofenoxim, bromoxynil, butachlor, butylate, cafenstrole, carbetamide, chlomethoxyfen, chloramben, chloridazon, chlorimuron(-ethyl), chlornitrofen, chlorsulphuron, chlortoluron, cinmethylin, cinosulphuron, clethodim, clodinafop(-propargyl), clomazone, clopyralid, clopyrasulphuron, cloransulam(-methyl), cumyluron, cyanazine, cycloate, cyclosulphamuron, cycloxydim, cyhalofop(-butyl), 2,4-D, 2,4-DB, 2,4-DP, desmedipham, di-allate, dicamba, diclofop(-methyl), difenzoquat, diflufenican, dimefuron, dimepiperate, dimethachlor, dimethametryn, dimethenamid, dinitramine, diphenamid, diquat, dithiopyr, diuron, dymron, EPTC, esprocarb, ethalfluralin, ethametsulphuron(-methyl), ethofumesate, ethoxyfen, etobenzanid, fenoxaprop(-ethyl), flamprop(-isopropyl), flamprop(-isopropyl-L), flamprop(-methyl), flazasulphuron, fluazifop(-butyl), flumetsulam, flumiclorac(-pentyl), flumioxazin, flumipropyn, fluometuron, fluorochloridone, fluoroglycofen(-ethyl), flupoxam, flupropacil, flurenol, fluridone, fluroxypyr, flurprimidol, flurtamone, fomesafen, glufosinate(-ammonium), glyphosate(-isopropylammonium), halosafen, haloxyfop(-ethoxyethyl), hexazinone, imazamethabenz(-methyl), imazamethapyr, imazamox, imazapyr, imazaquin, imazethapyr, imazosulphuron, ioxynil, isopropalin, isoproturon, isoxaben, isoxaflutole, isoxapyrifop, lactofen, lenacil, linuron, MCPA, MCPP, mefenacet, metamitron, metazachlor, methabenzthiazuron, metobenzuron, metobromuron, metolachlor, metosulam, metoxuron, metribuzin, metsulphuron(-methyl), molinate, monolinuron, naproanilide, napropamide, neburon, nicosulphuron, norflurazon orbencarb, oryzalin, oxadiazon, oxyfluorfen, paraquat, pendimethalin, phenmedipham, piperophos, pretilachlor, primisulphuron(-methyl), prometryn, propachlor, propanil, propaquizafop, propyzamide, prosulphocarb, prosulphuron, pyrazolate, pyrazosulphuron(-ethyl), pyrazoxyfen, pyributicarb, pyridate, pyrithiobac(-sodium), quinchlorac, quinmerac, quizalofop(-ethyl), quizalofop(-p-tefuryl), rimsulphuron, sethoxydim, simazine, simetryn, sulcotrione, sulphentrazone, sulphometuron(-methyl), sulphosate, tebutam, tebuthiuron, terbuthylazine, terbutryn, thenylchlor, thiafluamide, thiazopyr, thidiazimin, thifensulphuron(-methyl), thiobencarb, thiocarbazil, tralkoxydim, tri-allate, triasulphuron, tribenuron(-methyl), triclopyr, tridiphane, trifluralin and triflusulphuron.
A mixture with other known active compounds such as fungicides, insecticides, akaricides, nematicides, bird repellants, plant nutrients and soil conditioners is also possible.
The active compounds can be applied as such, in the form of their formulations or the use forms prepared therefrom by further dilution, such as ready-to-use solutions, suspensions, emulsions, powders, pastes and granules. The application is effected in the customary manner, for example by pouring, spraying, atomizing or broadcasting.
The active compounds according to the invention can be applied before or after plant emergence. They may also be incorporated into the soil prior to planting.
The application rate of active compound may vary within a substantial range. It depends essentially on the nature of the desired effect. In general, the application rates are between 1 g and 10 kg of active compound per hectare of ground surface, preferably between 5 g and 5 kg per ha.